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After I posted Tuesday's newsletter about how I hit an "invisible wall" at the edge of a map of my understanding, I came across these two familiar quotes: 1. "A

The thermometer read 19 degrees. The wind whipped louder than waves crashing on a beach. And I was zipped tight in a sleeping bag on top of a mountain. Action carried me away from comfort, and it was the only thing that could bring me back.  I wanted nothing more than a hot breakfast by t

Thirty-seven thousand Americans died in car accidents in 1955, six times today’s rate adjusted for miles driven. Ford began offering seat belts in every model that year. It was a $27 upgrade, equivalent to about $190 today. Research showed they reduced traffic fatalities by nearly 70%. But only 2% of customers opted for the upgrade. Ninety-eight percent of buyers preferred to remain at the mercy of inertia. Things eventually changed, but it took decades. Seatbelt usage was still under 15% in the early 1980s. It didn’t exceed 80% until the early 2000s – almost half a century after Ford offered them in all cars. It’s easy to underestimate how social norms stall change, even when the change is an obvious improvement. One of the strongest forces in the world is the urge to keep doing things as you’ve always done them, because people don’t like to be told they’ve been doing things wrong. Change eventually comes, but agonizingly slower than you might assume. Dunkirk was a miracle. More than 330,000 Allied soldiers, pinned down by Nazi attacks, were successfully evacuated from the beaches of France back to England, ferried by hundreds of small civilian boats. London broke out in celebration when the mission was completed. Few were more relieved than Winston Churchill, who feared the imminent destruction of his army. But Edmund Ironside, commander of British Home Forces, pointed out that if the Allies could quickly ferry a third of a million troops from France to England while avoiding aerial attack, the Germans probably could, too. Churchill had been holding onto hope that Germany couldn’t cross the Channel with an invasion force; such a daring mission seemed impossible. But then his own army proved it was quite possible. Dunkirk was both a success and a foreboding. Your competitors can probably innovate and execute as well as you can. So every time you uncover a new talent you’re proud of, temper your thrill with the acceptance that other people who want to win as badly as you probably aren’t far behind. Notorious BIG once casually mentioned that he began selling crack in fourth grade. He explained: They [teachers] was always like, “Take the talent that you have and think of something that you can do in the future with it.” And I was like, “Well, I like to draw.” So what could I do with drawing? What am I gonna be, an art dealer? I’m not gonna be that type. I was thinking maybe I can do big billboards and shit. Like commercial art. And then after that I got introduced to crack. Haha, now I’m thinking, commercial art?! Haha. I’m out here for 20 minutes and I can make some real, real money, man. Incentives drive everything, and most of us underestimate what we’d be willing to do if the incentives were right. Before launching themselves into space on rockets, NASA astronauts ran tests in high-altitude hot-air balloons. A balloon flight on May 4th, 1961, took American Victor Prather to 113,720 feet, scraping the edge of space. The goal was to test NASA’s new spacesuit. The flight was a success. The suit worked beautifully. As Prather descended back to earth, he opened the faceplate on his helmet when he was low enough to breathe on his own. He landed in the ocean as planned, but there was a small mishap: Prather slipped from his craft while connecting himself to the rescue helicopter’s line, falling into the ocean. The spacesuit should have been watertight and buoyant. But since Prather had opened his faceplate, he was now exposed to the elements. Water rushed into his suit. Prather drowned. Think of how much planning goes into launching someone to space. So much expertise, so many contingencies. So many what if’s and what then’s. Every detail is contemplated by thousands of expert workers. But even then – despite so much planning – a tiny thing no one had considered invites catastrophe. As Carl Richards says, risk is what’s left when you think you’ve thought of everything. When Barack Obama discussed running for president in 2005, his friend George Haywood – an accomplished investor – gave him a warning: the housing market was about to collapse, and would take the economy down with it. George told Obama how mortgage-backed securities worked, how they were being rated all wrong, how much risk was piling up, and how inevitable its collapse was. And it wasn’t just talk: George was short the mortgage market. Home prices kept rising for two years. By 2007, when cracks began showing, Obama checked in with George. Surely his bet was now paying off? Obama wrote in his memoir: George told me that he had been forced to abandon his short position after taking heavy losses. “I just don’t have enough cash to stay with the bet,” he said calmly enough, adding, “Apparently I’ve underestimated how willing people are to maintain a charade.” Irrational trends rarely follow rational timelines. Unsustainable things can last longer than you think. When the Black Death plague entered England in 1348, the Scots up north laughed at their good fortune. With the English crippled by disease, now was a perfect time for Scotland to stage an attack on its neighbor. The Scots huddled together thousands of troops in preparation for battle. Which, of course, is the worst possible move during a pandemic. “Before they could move, the savage mortality fell upon them too, scattering some in death and the rest in panic,” historian Barbara Tuchman writes in her book A Distant Mirror. There’s a powerful urge to think risk is something that happens to other people. Other people get unlucky, other people make dumb decisions, other people get swayed by the seduction of greed and fear. But you? Me? No, never us. False confidence makes the eventual reality all the more shocking. Some are more susceptible to risk than others, but no one is exempt from being humbled. Dr. Dan Goodman once performed surgery on a middle-aged woman whose cataract had left her blind since childhood. The cataract was removed, leaving the woman with near-perfect vision. A miraculous success. The patient returned for a checkup a few weeks later. The book Crashing Through writes: Her reaction startled Goodman. She had been happy and content as a blind person. Now sighted, she became anxious and depressed. She told him that she had spent her adult life on welfare and had never worked, married, or ventured far from home – a small existence to which she had become comfortably accustomed. Now, however, government officials told her that she no longer qualified for disability, and they expected her to get a job. Society wanted her to function normally. It was, she told Goldman, too much to handle. Every goal you dream about has a downside that’s easy to overlook. Historian John Meecham writes: When we condemn [the past] for slavery, or for Native American removal, or for denying women their full role in the life of the nation, we ought to pause and think: What injustices are we perpetuating even now that will one day face the harshest of verdicts by those who come after us? This applies to so many things. What is the modern version of cigarettes, which were doctor-recommended just a few generations ago? We didn’t know dinosaurs existed 200 years ago, which makes you wonder what else is out there that we’re oblivious to today. What company is the modern Enron, so obviously a fraud? What do most people – not a few wackos, but most of us – believe that will look something between hilarious and disgraceful 100 years from now? A lot of history is just gawking at how wrong, how blind, people can be. Disastrously wrong, embarrassingly blind. Millions of people, all at the same time. When you then realize that today will be considered history in a few generations … oh dear. It’s unpleasant. But also fascinating. Apollo 11 was the first time in history humans visited another celestial body. You’d think that would be an overwhelming experience – literally the coolest thing any human had ever done. But as the spacecraft hovered over the moon, Michael Collins turned to Neil Armstrong and Buzz Aldrin and said: It’s amazing how quickly you adapt. It doesn’t seem weird at all to me to look out there and see the moon going by, you know? Three months later, after Al Bean walked on the moon during Apollo 12, he turned to astronaut Pete Conrad and said “It’s kind of like the song: Is that all there is?” Conrad was relieved, because he secretly felt the same, describing his moonwalk as spectacular but not momentous. Most mental upside comes from the thrill of anticipation – actual experiences tend to fall flat, and your mind quickly moves on to anticipating the next event. That’s how dopamine works. If walking on the moon left astronauts underwhelmed, what does it say about our own earthly goals and expectations? John Nash is one of the smartest mathematicians to ever live, winning the Nobel Prize. He was also schizophrenic, and spent most of his life convinced that aliens were sending him coded messages. In her book A Beautiful Mind, Silvia Nasar recounts a conversation between Nash and Harvard professor George Mackey: “How could you, a mathematician, a man devoted to reason and logical proof, how could you believe that extraterrestrials are sending you messages? How could you believe that you are being recruited by aliens from outer space to save the world?” Mackey asked. “Because,” Nash said slowly in his soft, reasonable southern drawl, “the ideas I had about supernatural beings came to me the same way that my mathematical ideas did. So I took them seriously.” This is a good example of a theory I have about very talented people: No one should be shocked when people who think about the world in unique ways you like also think about the world in unique ways you don’t like. Unique minds have to be accepted as a full package. More: The Psychology of Money Five Lessons From History Death, Taxes and a Few Other Things

I collect books like the last one was printed yesterday . I can never have too many.  When my wife and I moved to our new home last year, I decided it was time to buy new book shelves. I wanted a matching set, and I wanted enough shelf space to hold my ever expanding collection. 

Here are my 10 best survival tips

I. A few months ago, I learned about Laszlo Polgar, the man who trained all three of his daughters to be chess grandmasters. He claimed he could make any child a genius just by teaching them using …

This is arguably the most important short reading I’ve done in a while. - Tim Ferriss

What I actually do all day

This Minyanville  article  written by Jeff Saut covers Peter Lynch's "cocktail party" theory. It's from the book One Up on Wall Street .  ...

When a crisis looms, first choose your group. The bigger the crisis, the less likely you are to survive it alone. Find people that you want to be with, then agree who does what. "I used to think I was not much good in a crisis, but over the years, I have realized there is no such thing as being individually good or bad in a crisis. Humans either deal with crises in effective groups, or not at all"

Last week I stumbled across the book Annotation, written by Remi Kalir and Antero Garcia. As the title suggests, the book is all about the history and practices of annotating texts. And probably be…

Two years ago, frustrated with a long list of unfulfilled project ideas in my phone notes, I decided to give myself one week to try each idea out in its tiniest form.

The memo below was sent to the team at Tiny Speck, the makers of Slack, on July 31st, 2013. It had been a little under seven months since…

Which path are you on? Tony Robbins explains there are 3 paths in life. Which one are you on?

“Not to eat but to think.”

In my writing on technology and culture I try to be judicious about citing scientific studies. The issues involved in our ongoing wrangling with digital innovations are subtle and often deeply human. Attempts to exactly quantify what we're gaining and losing through our screens can at times feel disconcertedly sterile. All that being said, however,

What I learned building an eight-figure candle business

How you respond to change makes all the difference when dealing with the unexpected. To keep moving in a direction you can be proud of, reprogram your thinking.

Daily notes as a frictionless default input for personal knowledge management systems

Seriously, it’s really weird. But it’s helped me for 25 years!

Even the most experienced writers can feel intimidated by editorial work, with its arcane rules and secret symbols. Here, I hope to demystify the process and prove that you can effectively edit your own work even if you've no idea what a dangling participle is and couldn't confidently identify an en

Most are probably unaware of the effort involved in maintaining a personal website or of the benefits that result.

Reading is a good thing. A good thing too many people don’t do enough of (or any of it all…) So obviously doing lots of it is good, right? This is why people try to figure out how to speed read (a scam, I say!). This is why they show off their huge libraries (guilty!). This is why they listen to audiobooks at 2x or 3x speed.  “Less is more? Quality over quantity? Not with books!”  But not all reading is created equal. As Epictetus said, “I cannot call somebody ‘hard-working’ knowing only that they read.” He said he needed to know what and how they read. Sure, reading is better than a lot of other activities, but you can still do it poorly or for poor reasons. “Far too many good brains,” Seneca said, “have been afflicted by the pointless enthusiasm for useless knowledge.” To be a great reader, it is not enough that you read, it’s how you read. These 13 strategies by no means make a complete list, but if you implement even a couple of them, I’m comfortable guaranteeing you’ll not only be a better reader for it, but a better person too. Stop Reading Books You Aren’t Enjoying  If you find yourself wanting to speed up the reading process on a particular book, you may want to ask yourself, “Is this book any good?” You turn off a TV show if it’s boring. You stop eating food that doesn’t taste good. You unfollow people when you realize their content is useless. Life is too short to read books you don’t enjoy reading. My rule is one hundred pages minus your age. Say you’re 30 years old—if a book hasn’t captivated you by page 70, stop reading it. So as you age, you have to endure crappy books less and less. Read Like A Spy One of the most surprising parts of Seneca’s writing is how that avowed Stoic quotes Epicurus, the founder of Epicureanism. Even Seneca knew this was strange as each time he did so in his famous Letters, he felt obliged to preface or explain why he was so familiar with the teachings of a rival school. His best answer appears in Letter II, On Discursiveness in Reading, and it works as a prompt for all of us in our own reading habits. The reason he was so familiar with Epicurus, Seneca wrote, was not because he was deserting the writings of the Stoics, but because he was reading like a spy in the enemy’s camp. That is, he was deliberately reading and immersing himself into the thinking and the strategies of those he disagreed with. To see if there was anything he could learn and, of course, to bolster his own defenses. Keep A Commonplace Book In his book, Old School, Tobias Wolf’s semi-autobiographical character takes the time to type out quotes and passages from great books to feel great writing come through him. I do this almost every weekend in what I call a “commonplace book”— a collection of quotes, ideas, stories and facts that I want to keep for later. It’s made me a much better writer and a wiser person. I am not alone. In 2010, when the Reagan Presidential Library was undergoing renovation, a box labeled “RR’s desk” was discovered. Inside the box were the personal belongings Ronald Reagan kept in his office desk, including a number of black boxes containing 4×6 note cards filled with handwritten quotes, thoughts, stories, political aphorisms, and one-liners. They were separated by themes like “On the Nation,” “On Liberty.” “On War,” “On the People,” “The World,” “Humor,” and “On Character”. This was Ronald Reagan’s version of a commonplace book. Lewis Carroll, Walt Whitman, Thomas Jefferson all kept their own version of a commonplace book.  As Seneca advised, “We should hunt out the helpful pieces of teaching and the spirited and noble-minded sayings which are capable of immediate practical application–not far far-fetched or archaic expressions or extravagant metaphors and figures of speech–and learn them so well that words become works.” Re-Read The Masters You were in high school when you read The Great Gatsby for the first time. You were just a kid when you read The Count of Monte Cristo or had someone tell you the story of Odysseus.  The point is: You got it right? You read them. You’re done, right? Nope. We cannot be content to simply pick up a book once and judge it by that experience. It’s why we have to read and re-read. As Seneca put it, “You must linger among a limited number of master-thinkers, and digest their works, if you would derive ideas which shall win firm hold in your mind.” Because the world is constantly changing, we are changing, and therefore what we get out of those books can change. It’s not enough to read the classics once, you have to read them at every age, every era of your life. We never step in the same river twice, Marcus Aurelius said, and that’s why we must return again and again to the great works of history. Read Fiction There’s an interesting thread running through in the writings and teachings of Marcus Aurelius, Seneca, and Epictetus that can zip right past you if you aren’t reading closely. What is it? What did all these great men share? They heavily relied on plays, tragedies, satires, mythologies, and other works of fiction to clarify their thinking and their own writing. Epictetus draws on characters like Achilles and Agamemnon from the Iliad, Admetus from Euripides’ Alcestis, and a long list of others from Greek mythology. Marcus Aurelius quotes from the comedies of Aristophanes, the tragedies and plays of Euripides and Sophocles, and says we should read fiction “to remind us of what can happen, and that it happens inevitably—and if something gives you pleasure on that stage, it shouldn’t cause you anger on this one.” Seneca liked to quote the works of the great Roman poets [...]

Reggie Vanderbilt was born into a family of bitter feuds, fragile egos, and impossible expectations. Everything went downhill from there. When Reggie’s great-grandfather, Cornelius “Commodore” Vanderbilt died in 1877, the New York Daily Tribune wrote an editorial predicting the legacy of the world’s richest man: The Vanderbilt case is an impressive lesson in the folly of attempting to “found a family” upon no better basis than the possession of money. The ruling idea of the Old Commodore’s latter years was to amass a huge fortune which should stand for generations as a monument to the name of Vanderbilt, and make the head of the house a permanent power in American society. There is no country in the world where fortunes are made so quickly … and none in which inherited money has done so little for its possessors. The Vanderbilt money is certainly bringing no happiness and no greatness to its present claimants, and we have little doubt that in the course of a few years, it will go the way of most American fortunes; a multitude of heirs will have the spending of it, and it will be absorbed in the vast circulating system of the country. The plans of the dead railway king will come to naught; and if he ever revisits the earth to look after what he had so much at heart in his last years, he will be satisfied that the art of founding a family was one of the things that he did not know. This harsh opinion underestimated what was to come. Cornelius Vanderbilt left his heirs the inflation-adjusted equivalent of something like $300 billion. Within 50 years it was gone. In between sat three generations whose primary purpose was to compete on who could build the largest house and marry the bluest blood. The first heirs had some entrepreneurial sense of running the family business; over time the “family business” became insecurity and resentment. In 1875 an op-ed said socialites “devote themselves to pleasure regardless of expense.” A Vanderbilt responded that actually they “devote themselves to expense regardless of pleasure.” It was a game that couldn’t be won, so everyone lost. Reggie was one of the last Vanderbilts to inherit significant wealth. On his 21st birthday he received $12.5 million, or about $350 million in today’s dollars. Family biographer Arther Vanderbilt writes: Self-indulgent, lazy, lackadaisical, Reggie had absolutely no sense of responsibility or purpose other than to keep himself from being bored … [he was] never employed and never did a lick of work. Somewhat at a loss when asked his occupation, he usually responded, ‘Gentleman.’ … The only way Reggie could distinguish himself was to live the life of a rich playboy. And this he did with dedication and consummate skill. Reggie’s two loves were brandy and gambling. The first left him dead at age 45, with cirrhosis so severe the blood flow from his liver was cut off and pushed up to his esophagus, where the veins abruptly ruptured and left him choking in a pool of blood. The latter left him broke – after repaying debts Reggie’s will was nearly irrelevant, as he had nowhere near the amount of money promised to his heirs. Reggie’s grandson – Anderson Cooper – was one of the first Vanderbilts who was never promised dynastic wealth. It may have been a blessing. Cooper once said of inheritance: “I think it’s an initiative sucker. I think it’s a curse. From the time I was growing up, if I felt like there was some pot of gold waiting for me, I don’t know if I would have been so motivated.” It’s like he was the first Vanderbilt to be set free. – Money is fungible in the sense that my dollar bill is indistinguishable from your dollar bill. But the value people get out of a dollar varies wildly, even among people with the same income and net worth. I’m always interested in the difference between getting rich and staying rich. They are completely different things, and many of those skilled at the former fail at the latter. Part of this topic is knowing the difference between rich and wealthy. These definitions are my own, but here’s the distinction: Rich means you have cash to buy stuff. Wealth means you have unspent savings and investments that provide some level of intangible and lasting pleasure – independence, autonomy, controlling your time, and doing what you want to do, when you want to do it, with whom you want to do it with, for as long as you want to do it for. What I find fascinating are stories like the Vanderbilts, who were the richest people on earth but, by my definition, some of the least wealthy. Money to them was less of an asset and more of a social liability, indebting them to a status-chasing life that left most of them seemingly miserable. George Vanderbilt spent six years building the 135,000-square-foot Biltmore house – with 40 master bedrooms and a full-time staff of nearly 400 – but allegedly spent little time there because it was “utterly unaddressed to any possible arrangement of life.” The house nevertheless cost so much to maintain it nearly ruined Vanderbilt. Ninety percent of the land was sold off to pay tax debts, and the house was turned into a tourist attraction. There are so many similar stories from the Vanderbilt family that you begin to ask, “What was the point?” The point, as the New York Daily Tribune realized early on, was not to live a great life. It was to be rich – to be valued “upon no better basis than the possession of money.” Rather than using money to build a life, their life was built around money; rather than an asset, their inheritance was an insurmountable lifestyle debt, passed to the next generation until there was mercifully nothing left. In his 1903 book The Quest for the Simple Life, William Dawson writes: The thing that is least perceived about wealth is that all pleasure in money ends at the point where economy becomes unnecessary. The man who can buy anything he covets, without any consultation with his banker, values nothing that he buys. Nassim Taleb echoes a similar point when he says, “The record shows that, for society, the richer we become, the harder it is to live within our means. Abundance is harder for us to handle than scarcity.” You become a victim of your own success. The Vanderbilts are an extreme example, but I think they were just a magnified version of what so many regular people deal with today. Average household incomes adjusted for inflation have more than doubled in the last 70 years, but it doesn’t feel that way because expectations have more than doubled. Part of the reason home affordability is lower today than in previous generations is because the average new home is a third larger than it used to be; millions of Americans haven’t saved enough to retire, but just a few generations ago the entire concept of retirement was a dream. I want to be rich, because I like nice stuff. But what I value far more is to be wealthy, because I think independence is one of the only ways money can make you happier. The trick is realizing that the only way to maintain independence is if your appetite for stuff – including status – can be satiated. The goalpost has to stop moving; the expectations have to remain in check. Otherwise money has a tendency to be a liability masquerading as an asset, controlling you more than you use it to live a better life.

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My Schedule Should Be Terrible... I should have an overwhelming, Malox-guzzling, stress-saturated schedule. Here's why: I'm a graduate student in a demanding program. I'm working on several research papers while also attempting to nail down some key ideas for my dissertation. I'm TA'ing and taking courses. I maintain this blog. I'm a staff writer for